Synthesis and Tastes of Some Flavanone- and Dihydrochalcone Glycosides

Naringenin-7-β-maltoside (I), -7-β-cellobioside (II), -7-β-lactoside (III), -7-β-melibioside (IV) and hesperetin-7-β-[d-galactosyl (α 1→2) d-glucoside] (V), -7-β-[d-glucosyl (β 1→2) d-galactoside] (VI) and -7-β-melibioside (VII) were prepared by the coupling of naringenin or hesperetin with the acetobromo derivatives of appropriate disaccharides followed by removal of the protecting acetyl groups. Narigenindihydrochalcone-4′-β-kojibioside (VIII), -4′-β-maltoside (IX), -4′-β-cellobioside (X), -4′-β-lactoside (XI), -4′-β-melibioside (XII) and hesperetindihydrochalcone-4′-β-[d-galactosyl (α 1→2) d-glucoside] (XIII), -4′-β-sophoroside (XIV) and -4′-β-melibioside (XV) were synthesized by catalytic reduction of the appropriate flavanone-7-β-glycosides. Among the compounds synthesized, IX and X are 4 and 8 times as sweet as sucrose on the basis of percentage concentration, respectively, but the others are tasteless.